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Who should the A’s target for an extension?

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And what a potential extension will look like.

MLB: Baltimore Orioles at Oakland Athletics Ed Szczepanski-USA TODAY Sports

Since Dave Kaval took the reins, things have been different. We’ve got an upgraded home yard, a location for a new one, and an overall energy around the organization that hasn’t been present in recent years.

Another major change is the organization’s approach to young players. Gone are the days where a good player being traded is a certainty, in are the days where we can reasonably dream of some of these guys being around long term. The A’s are hoping to enter their new stadium with a core that’s breaking into the league now.

The A’s often deviate from what they say, but Kaval is a doer, a man of his word and we have no reason to think the A’s don’t intend on keeping their young stars around for the long haul. Should it happen, will it happen, and who are the potential candidates? Let’s explore.

Extensions are getting rarer

It takes two to tango, and the player side of the extension equation has shown reluctance in recent years. Guys like Francisco Lindor and Kris Bryant have declined security for upside, turning down money now for the chance to make much more in free agency.

It’s not a hard and fast rule, and it’s too recent to know how pervasive it will be. It does appear that a player might not take an extension even if it’s at a fair market rate that might normally get the job done. Something to chew on.

Should the A’s try?

The answer is yes. Of course we want our favorite players around after not having that luxury for a few decades.

A word of caution, though. Extensions typically do work fairly well. Unlike free agency, which requires bidding wars for players who are by definition past their prime, extensions afford teams the luxury of signing younger players long term without other teams driving up the dollar amount.

That said, extensions do fail. You’re an A’s fan, you know this. Here’s every extension of four years or longer since the end of the 2015 season via MLB Trade Rumors wonderful extension tracker.

Extensions since 2015

Date Player Team Pos Years Dollars (millions) Service time 2017 bWAR
Date Player Team Pos Years Dollars (millions) Service time 2017 bWAR
09/22/2017 Tucker Barnhart CIN C 4 16 3.075 3.4
06/07/2017 Jean Segura SEA SS 5 70 4.13 3.1
04/03/2017 Stephen Piscotty STL RF 6 33.5 1.076 0.6
04/02/2017 Roberto Perez CLE C 4 9 2.083 0.8
03/30/2017 Rougned Odor TEX 2B 6 49.5 2.121 -0.2
03/28/2017 Jose Ramirez CLE 2B / SS / 3B / LF 5 26 2.074 6.9 (nice)
03/21/2017 Tim Anderson CWS SS 6 25 0.115 0.9
03/14/2017 ⇑Kevin Kiermaier TAM CF 6 53.5 2.131 5.1
02/02/2017 Carlos Martinez STL SP 5 51 3.073 3.2
01/17/2017 Wil Myers SDG 1B 6 83 3.104 2.1
01/16/2017 Danny Duffy KAN SP 5 65 5.085 3.3
12/23/2016 ⇑Ender Inciarte ATL LF / CF / RF 5 30.525 2.157 3
12/15/2016 Odubel Herrera PHI CF 5 30.5 2 2.2
05/10/2016 Stephen Strasburg WAS SP 7 175 5.118 6.7
04/09/2016 Brandon Belt SFO 1B 6 79 4.128 3
04/03/2016 Gregory Polanco PIT RF 5 35 1.103 0
03/02/2016 Kolten Wong STL N/A 5 25.5 2.045 1.9
03/01/2016 Salvador Perez KAN C 5 52.5 4.05 2.5
01/14/2016 ⇑Dee Gordon MIA 2B 5 50 3.154 3.1
11/17/2015 Brandon Crawford SFO SS 6 75 4.094 2.1

Some of these guys have been awesome, some have been disasters. It’s not a sure thing, but it can be an amazing thing. The A’s will have to choose wisely and get lucky - it’s certainly not all skill.

The guys to pay closest attention to are those with less than a year or two of service time. The A’s candidates for extensions are all supremely young and would fit the mold of a Tim Anderson kind of extension - cheaper for the franchise because the player is so far away, and signing that early extension mitigates the players risk.

As detailed above, players are more reluctant now to do that than before, so it might take a few more dollars to get the job done, but the Tim Anderson deal is still a good jumping off point.

Who are the candidates?

These guys are not surprising, not even a little bit. But they’re fun to talk about so huzzah!

Matt Olson

You know what Olson did, and it was glorious. If he’s anywhere near as good as he was this season, he’ll be a gamechanger, one of the better hitters in the game and a guy who changes a whole lineup’s complexion.

The issues? We really don’t know what exactly Matt Olson is. He’s not going to hit dingers at a record breaking pace forever, and his small sample told us he can be great. Will he be great at scale? That’s of course the crux of the issue of extensions, but it’s particularly germane here.

If someone is going to bet on himself, it’s a guy who made major league pitchers look like little leaguers for a month and a half. Olson is a guy who would make excellent money in arbitration with his power, and waiting till free agency is more tenable with the knowledge of a potentially huge payoff coming in just a few years time.

Matt Chapman

So long as Matt Chapman is making ridiculous plays in the green and gold, life is good.

Defensive stats can vary year by year, but health provided, Chapman will be a value add for the A’s for years to come. With the ridiculous amount of foul territory in Oakland and the typical groundball nature of the A’s staff, even if Chapman doesn’t hit, he’s a good piece to have.

He should hit, at least enough and maybe much more.

The surprise contender

In the event that both Chapman and Olson are reluctant to sign an early extension, the A’s have other, less conventional options. Namely, the Jonathan Singleton route.

This is rare, and for my money underutilized, especially for a low budget team like the A’s.

As a reminder, Jonathan Singleton was a top prospect who signed a contract extension before even making his big league debut. It gave Singleton financial security he wouldn’t have otherwise have had, and should he have produced, it would have been an extremely team friendly deal.

These contracts are rare. Singleton is basically the only true example I can drum up, making it an extremely unlikely scenario for the A’s. But the A’s are weird, so let’s imagine.

Franklin Barreto

It’s been tough sledding for the top A’s prospect since hitting AAA. Barreto’s strikeout rate has skyrocketed and his defense has stagnated, making him no sure thing at the big league level.

He’s got youth on his side, and the upside is still in the form of his lightning hands. However there’s no doubt his stock has slipped, and of the group listed, he’s likely the furthest from a sure thing.

Barreto is unlike Singleton in that he has yet to prove himself at the AAA level. Even with that success, Singleton fizzled out so Barreto would prove a risk.

_____

The last guy on this list isn’t all that serious of an option, at least not yet. When the A’s talk about extending their youngsters this offseason, they’re referring to Matt Olson and Matt Chapman, two guys who would be delightful to have going into the new stadium.

Of course, the A’s aren’t hoping to extend one or two guys. It might start small in scale, but the goal is to eventually hold onto their valuable fan favorites for the long haul. How should they start that process?